7 Tips for Surviving a Kinky First Date

What questions should you be asking on a kinky first date?

First dates suck

First dates are plagued with awkward pauses, conversational blunders, and tons of pressure. All you want to do is impress your date, who is someone you barely know. You don’t understand why you never seem to have a good first date. You see all your kinky friends in great long-term relationships. They have flaws and even screw up sometimes just like you do. How is it that they’ve made it past their first dates when you continue to fail?

The fact is, first dates and established relationships are very different. When you have an ongoing relationship, you have license to mess things up occasionally. Unfortunately, during a first date, you don’t have a large margin for error. If you botch your date, you might not get another chance.

First dates suck. But don’t fret! I’m going to give you seven easy tips you can apply to win at your next first date.

1. Understand when NOT to talk about kink

Talking about kink and sex with a new potential partner should not be taboo. We always want to be safe when it comes to sex, and we want to make sure we are not wasting our time dating someone we are not compatible with.That being said, discussing kink and sex too early on in the game can give your date the impression you are only interested in them for sex.

Your kinky date is probably fully aware that you engage in kinky activities and have sex. They are not oblivious to the fact that you eventually want to engage in kink and/or other sexual acts with them. Kinky people are going to be more open and take less offense to having blunt sexual conversations than vanillas. Your date is in all likelihood just as adventurous as you. However, diving into what fetishes you have in common and how you want to fuck them is not going to go over well on a first date.

Balance and patience are the keys to having an intriguing and meaningful conversation with a date. Part of that balance is making sure you bring the subject of kink up at an appropriate time and place. Your first date may not be that time.

If your date is comfortable and wants to talk about kink and sex, they will bring it up. Let them initiate this discussion if possible. If they don’t bring the conversation up and you want to, ask yourself these things first:

Are you about to ask questions that might be answered on your date’s profile? – If you are not sure, go read the profile. People get very annoyed answering questions or addressing topics that are clearly stated in their profiles. Before going on a date, do your research.

Are you on a date in a place where your conversation can be easily overheard? – If so, talking about kink and sexual preferences should probably be saved for another date. The last thing you want to do is out your date or make them uncomfortable.

If you answered no to both those questions and are curious about your date’s kinks, the best way to approach the conversation is to ask: “How did you get into kink?” This will allow them to decide how much they are comfortable talking about now. Their answer might be something short like, “A friend took me to a party once,” or you might get a forty-five minute story of all their explorations. You will be amazed at the things people will talk about if you ask the right question and listen.

If your date gives a short answer and doesn’t broach the subject again, drop the conversation. If the two of you decide to explore more dates, there will be plenty of time to converse about kink and sex. Sometimes the best thing to do on a first date is to back burner the sex conversation until both of you are in a comfortable place to bring it up. First dates are stressful enough; you don’t need to add more anxiety by being fixated on having “the conversation.” If you are unsure what questions you should be answering (and asking), check out my free report: 20 Questions You Should Be Asking on Your First Date.

2. Act your age

Unless your date has blatantly told you they are into littles, you need to act like a mature adult. Grownups are not late, not intoxicated, and don’t make offensive jokes.

Not acting your age is the best way to put yourself on the fast track to No Second Dateville. When you are on a first date, you want to be yourself, but you also want to present the best you possible. Make sure to bring your manners and common sense with you.

3. Stop trying to prove yourself

When we are dating, we get caught up on trying to show a date we are good enough. We sit at the dinner table thinking, “How am I going to mess this up?”

If you lack confidence in yourself, you will appear desperate or overbearing. People make up for their lack of confidence in two ways: They either become a pathetic doormat or an overbearing asshole.

Doormat – You become timid. You start second guessing your statements. You over-compliment your date and put them on a pedestal. This is a huge turn off for those who are submissive identified and can even be problematic for dominant ones. Remember dominant individuals want someone who is going to submit to them and not someone who is a doormat.

Asshole – You spend the entire time talking about yourself. You don’t spend time getting to know your date. You dwell on all your achievements and what your aspirations are. In the end, they will feel like you would have been better off going on a date with yourself.

You should cultivate an optimistic and curious mindset.

When your date asks questions about your life, talk in a positive and self-assured way. However, you should be asking just as many, if not more, questions than they are. Letting them talk will take a lot of pressure off of yourself. Ask your date profound questions that will screen them for the qualities you desire in a partner. There are 20 questions you should be asking on your first date.

As your discussion goes on, add relevant stories and jokes. Describe your points of view on the current topic. Occasionally give your date a compliment when they have earned it, but don’t over do it. One genuine compliment carries far more weight than tons of trivial ones.

You should be asking questions that will fill you in on what your date’s interests are. And not just their kinky interests! You should inquire about their past experiences and future dreams.This will help you judge their compatibility and if they are going to be worthy of future investment. When your date is talking, you should be learning about them. But at the same time, you shouldn’t be only asking questions. Make sure you are filling your date in on who you are as well.

When engaging your date in conversation, it’s good practice to occasionally point out things you have in common by saying “me too.” But make sure not to over do it. If you start pointing out that you both have noses and wear shirts, you are going to come off as creepy. If you two have similarities and a good connection, your date will notice on their own.

You also need to be authentic. Don’t aimlessly agree with everything your date says. They will have far more regard for you if you demonstrate (respectfully!) that you have independent or differing views.

Finally, stay away from trying to fill every bit of silence. If there are a few moments of silence, that’s okay. It is better to have a little quiet than to just ramble.

4. Avoid seeming needy and creepy

You might think calling someone slave, Master, or Mistress is flattering. You might also think bringing up your views on children and marriage is a good way to be honest and to let your date figure out if you are a good catch. You would be wrong. Let me say this again, this is wrong! Talking about this stuff on a first date is some of the worst dating advice someone could give you.

Most people go out on dates to have fun and to learn a little about a prospective partner. Even if they strive to one day be someone’s Dominant and have many babies, they don’t want to have this conversation with someone who is basically a stranger. Talking about power dynamics, marriage, children and committing your life (in any way) to them, is inappropriate for a first date.

By trying to push these topics so soon, you’re actually sabotaging your first date. Not because of what your desires are (your date may have the same ones), but because you are coming across as desperate and creepy.

My advice, skip conversations about kids and marriage when you are on your first date.

Don’t call people slave, Master, Mistress, etc. without a discussion. Don’t start acting “Domly” or “subby” and don’t expect your date to act in a certain role. The purpose of a first date is to get a sense of chemistry between yourself and a potential partner and to determine whether there’s enough compatibility to meet for a second date.

5. Keep your hands to yourself (unless invited)

If you have been in the kink world for more than an hour, you know consent is a huge topic. It is harped on in almost every discussion regarding kinky play. There is far more of a focus on consent than in the vanilla pickup world. You know this, and so will your date.

In kinky dating, advances need to be handled in a way that your date doesn’t feel like you are overstepping their boundaries. This doesn’t mean not flirting, making a move or even going for that first date kiss. It means paying attention to your date’s expressed interest or lack thereof. It also means making sure to not push when your date says no.

Many people think touching a lot during the first date shows that you are interested. This is not always the case. If your date is not ready, you will appear inconsiderate and pushy. It may also give them the impression that you are touchy-feely on every date you go on, and this will make them feel less special. Kinky people may not be as put off by touch as vanilla people, but even kinksters don’t want to feel like another dessert on your buffet.

Keep physical touch friendly and welcoming. Reach across the table to hold your date’s hand. Take their hand when walking through a crowd. Don’t try putting your hand on their lap or try to touch genitals or breasts. Don’t constantly try to hang your arm around their neck or hold them next to you throughout the entire date.

Once touch feels natural and your date expresses desire in moving things forward, you can turn up the touch.

6. Dress for success, but not in excess

Obviously, you want to look your best, but a first date isn’t the time to try on a brand new dress or pair of shoes. A first date is already going to be nerve-wracking. Adding clothing you are uncomfortable in is only going to make the situation worse.

Aside from comfort, use common sense about what you should wear. What you wear to an upscale restaurant should be very different than what you wear for a picnic and hike. When in Rome, do as the Romans do.

And for crying out loud, don’t go out to a vanilla restaurant in fetish clothing. This should be a no-brainer but people do it all the time. If you are in a vanilla environment, you should dress accordingly. Even if your date is very openly kinky, they will not appreciate you making a scene at a restaurant. Your assless chaps or transparent latex dress is not appropriate for a vanilla setting.

If you are meeting up at a scene party, more power to you. Just be sure to check what type of party you are going to and what the typical attire is for that particular event.

7. Determine where you stand

No matter what, first dates are always going to start off a bit awkward. The good news is as long as you follow the above tips, that awkwardness will decline as the date continues.

After a date, both parties always wonder: “Did the other person enjoy the date?” Most of the time this question goes unanswered. Why? Because neither party is willing to ask!

There’s a simple solution: If you had a good time with your date and would like to go out again, tell them! Don’t wait to be asked or for your date to say something. Not only will they appreciate your honesty, but your answer will encourage them to do the same for you.

If you get a positive response, such as “I had a good time” or “It was fun,” great! Your date had a good time.

If they delay giving an answer, it means they’re wishy-washy about the experience. It doesn’t necessarily mean they had a bad time, but it probably means there are areas where you could improve. A good move here would be asking your date how you could make your next date better.

If your date doesn’t reply to your expression that you enjoyed the date, that’s a good sign that they are not interested. That sucks, but at least it saves you from wondering later.

Above all else, don’t second-guess yourself. If you feel like your date went well when you two went your separate ways, don’t speculate about it later. If you do, you will only start seeing negative things that were never there.

On the contrary, if something about your date didn’t feel right, listen to your inner self. Ask yourself why you are unsatisfied. If you were not into your date, that’s okay. If you think you messed up, take a little time think about it. Figure out what didn’t work before you go on your next date.

If there is a common pattern or reason why you are struggling with a first date, pinpoint it in order to work on resolving the issue.

You’re on the right track

Going on first dates can feel overwhelming and things might start to feel hopeless. This is normal. As frustrating as the dating game is, the good news is, you are on the right track. The best thing you can do is to keep trying. The more dates you go on, the more natural they will feel and the less nervous you will be. Most people have to go on tons of first dates before they find someone that they are compatible with. Just remember that it’s a waste of time and emotional energy to date people that you know you’re completely incompatible with.

By following these tips and keeping a positive outlook, you will find the partner you are looking for. Don’t forget to download my report on 20 Questions You Should Be Asking On a Kinky First Date. These questions will eliminate awkwardness while also helping you get to know the person sitting across the table.

What questions should you be asking on a kinky first date?

Cassie is a kinky, bisexual, poly chick. And a mother. Since 2008, she has been teaching and presenting on various relationship and kink-related subjects, and helping other kink and poly folk succeed in their dating lives.

Cassie is one of the co-founders of Touch of Flavor and handles all things media-relations-y.

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